methyl (2S,4aR,5S,8aS)-(-)-2-(tert-butyldiphenylsilyloxymethyl)-5-methyl-7-oxo-octahydroquinoline-1-carboxylate | 460054-20-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉类
• 英文名称: methyl (2S,4aR,5S,8aS)-(-)-2-(tert-butyldiphenylsilyloxymethyl)-5-methyl-7-oxo-octahydroquinoline-1-carboxylate
• 英文别名: methyl (2S,4aR,5S,8aS)-2-[[tert-butyl(diphenyl)silyl]oxymethyl]-5-methyl-7-oxo-2,3,4,4a,5,6,8,8a-octahydroquinoline-1-carboxylate
• CAS: 460054-20-0
• 化学式: C₂₉H₃₉NO₄Si
• 分子量: 493.718
• InChiKey: FDKKSQQABCLWHP-ABMRFVCESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.78
• 重原子数：
  35
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl (2S,4aR,5S,8aS)-(-)-2-(tert-butyldiphenylsilyloxymethyl)-5-methyl-7-oxo-octahydroquinoline-1-carboxylate 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 以67%的产率得到methyl (2S,4aR,5S,8aS)-(-)-2-(hydroxymethyl)-5-methyl-7-oxo-octahydroquinoline-1-carboxylate
  参考文献：
  名称：

  Stereodivergent Process for the Synthesis of the Decahydroquinoline Type of Dendrobatid Alkaloids

  摘要：

  A flexible and stereodivergent synthesis of the cis- and trans-fused 2,5-disubstituted octahydroquinolinone ring systems bearing all four stereogenic centers for the synthesis of the decahydroquinoline type of dendrobatid alkaloids has been achieved. The strategy involves stereoselective and stereodivergent construction of 2,3,6-trisubstituted piperidine ring systems using the Michael type of conjugate addition reaction to the enaminoesters 1 and 3, the intramolecular aldol type of cyclization reaction of keto aldehydes 11 and 12, and ring-closing metathesis of 21 as key steps.

  DOI：

  10.1021/jo025929b
• 作为产物：
  描述：

  2-O-ethoxycarbonyl 1-O-methyl (2R,3S,6S)-6-[[tert-butyl(diphenyl)silyl]oxymethyl]-3-ethenylpiperidine-1,2-dicarboxylate 在 lithium hydroxide 、 sodium periodate 、 copper(l) iodide 、 四氧化锇 、 silver benzoate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 、 N,N'-羰基二咪唑 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 乙醚 、 二氯甲烷 、 水 、 苯 为溶剂， 反应 100.0h， 生成 methyl (2S,4aR,5S,8aS)-(-)-2-(tert-butyldiphenylsilyloxymethyl)-5-methyl-7-oxo-octahydroquinoline-1-carboxylate
  参考文献：
  名称：

  Stereodivergent Process for the Synthesis of the Decahydroquinoline Type of Dendrobatid Alkaloids

  摘要：

  A flexible and stereodivergent synthesis of the cis- and trans-fused 2,5-disubstituted octahydroquinolinone ring systems bearing all four stereogenic centers for the synthesis of the decahydroquinoline type of dendrobatid alkaloids has been achieved. The strategy involves stereoselective and stereodivergent construction of 2,3,6-trisubstituted piperidine ring systems using the Michael type of conjugate addition reaction to the enaminoesters 1 and 3, the intramolecular aldol type of cyclization reaction of keto aldehydes 11 and 12, and ring-closing metathesis of 21 as key steps.

  DOI：

  10.1021/jo025929b

文献信息

• Stereodivergent Process for the Synthesis of the Decahydroquinoline Type of Dendrobatid Alkaloids
  作者：Naoki Toyooka、Maiko Okumura、Hideo Nemoto

  DOI：10.1021/jo025929b

  日期：2002.8.1

  A flexible and stereodivergent synthesis of the cis- and trans-fused 2,5-disubstituted octahydroquinolinone ring systems bearing all four stereogenic centers for the synthesis of the decahydroquinoline type of dendrobatid alkaloids has been achieved. The strategy involves stereoselective and stereodivergent construction of 2,3,6-trisubstituted piperidine ring systems using the Michael type of conjugate addition reaction to the enaminoesters 1 and 3, the intramolecular aldol type of cyclization reaction of keto aldehydes 11 and 12, and ring-closing metathesis of 21 as key steps.